Something About the Chase
by minnellis
Summary: Eight times Dan Humphrey asked Katherine Pierce out and the one time she said yes. AU one shot.


She only agreed to accompany him to the local bar in Brooklyn because of her love for the drink. Dan was odd, that's what she knew of him. A freelance writer, he attended NYU while she spent her days lounging around her penthouse suite, perfectly content in living off of her father. Why go to school and work when your father was a wealthy Russian businessman?

Being a socialite in New York City, of course she knew the wild Serena van der Woodsen. Who didn't? And she supposed that was the girl to blame for introducing the two. After all they were stepsiblings, so she was easiest to put at fault. Katherine didn't commit the first meeting to memory simply because she doubted this man with the curly, dark mop on his head was even worth remembering. He stumbled over his words, made corny jokes, and seemed a little overwhelmed in just speaking with her. She was used to such attention, and therefore, wasn't exactly impressed.

Somehow, in her hazy recollection of that particular evening, she had agreed to accompany him to a small pub in Brooklyn. She only _actually_ ended up going because Serena forced her to by offering to buy her a new leather jacket, something Katherine couldn't refuse. Now she stood here with the boy next to her, both of them downing shot after shot, and she couldn't lie; this night was fun. Be it the Limoncello or the fact that her company was much less awkward with a few drinks in him, Katherine didn't completely, entirely regret coming.

Until Dan for some reason thought it would be a good idea to hop up on stage and start singing karaoke. It was an unknown song to her, but figuring it out didn't really matter. She could only stare with widened eyes as he proceeded to ask her out on a real date when the music faded into nothingness. With spotlights on them both now, she couldn't fathom that he would have ever had the guts to do that. It wasn't the liquor that made her cheeks warm up and without really giving him a proper answer she grabbed her jacket and casually strolled out of the bar. Katherine was pretty sure she could hear booing coming from inside. She didn't stop to investigate any further.

* * *

The next time he chose to embarrass her in public only happened a few days later, much to her displeasure. She had to drag herself out of bed while the sky was still bright and blinding, which the maid later told her was just 'sunlight'. Something Katherine obviously wasn't used to after a few years of being a night owl. The dark was simply more her thing. There was something happening at her father's office, a few magazine writers were stopping by, and she had to be there with her mother to promote "family". Something like that? She hadn't exactly been paying attention when it was explained, all she knew for certain was that she had to be there or she'd lose a credit card.

With large sunglasses on and the most reserved purple dress she owned, which still had a deep cut in the front, she made her way into the building behind her mother. Only to be met with an excited man pushing a mail cart. Her name was called, and she stumbled to a standstill. Turning her head with brows furrowed in confusion, she was met with the proud grin of Daniel Humphrey. This guy must have been everywhere, though when she asked he explained the details of his internship at her father's company. Katherine probably stopped listening about three quarters of the way through however, deciding it was time to catch up with her mom who was impatiently waiting at the elevator. That wasn't it though. Behind her she felt the slight bump of a mail cart and heard the resounding request of her needing to give his offer a second chance. He wanted her to take that date with him. And apparently he was going to assault her with a mail cart until she gave in. However it only served to make her laugh and really wake her up, something she could legitimately appreciate from him.

Finally reaching the elevator she turned on him and grabbed the other end of the cart. With a solid denial of the date she pushed the object back into his center, causing him to emit a low grunt of surprise and discomfort. Though as he rubbed his ribs he smiled at her. Elevator doors closing on them now, she could tell that was an expression of determination. He wasn't going to let this be over, and Katherine knew she would need to grab some coffee upstairs if she had any hope of dealing with what awaited her.

* * *

A couple of hours and cups of Joe later, the glasses were off and Katherine actually felt ready to meet the day. More specifically she was ready to meet Dan, who was probably still lurking around the office like a ninja and waiting for her. With each progressive heel click against the marble floor and each second passing without hearing that deep voice or feeling the smooth hardness of the mail cart against her back, she thought she may have been in the clear. He wasn't around; she could exit the building of her father's office peacefully and go home. Probably only to end up passing out right back into bed.

With a tiny, successful smirk at the thought of avoiding Dan she crossed over the threshold and spotted the limo off to the side. The man holding the back door open wasn't the usual driver however. It just had to be the man with the Muppet hair. Maybe it was silly of Katherine to have assumed she was in the clear _before_ reaching the penthouse. At this point, she was clearly underestimating the man. Slowly walking over she asked him what the hell did he think he was doing. It seemed he had gotten off of work just ten minutes before, so being out here when she was, was just merely coincidence. Although she was clever enough to know Dan was leaving nothing up to chance with her. He was the type; he was planning all of this out. And it made her wonder how much free time did he have on his hands to predetermine all of this.

His persistence and determination were things she could admire, since she could be equally as stubborn in getting what she desired. Plus she wanted him to stop nagging her. Those were the reasons she stood beside the opened limo door and offered him to get in the back.

Seducing random men could have been a second job for Katherine Pierce. She did it on a daily basis so inviting someone she barely knew, like Dan, for a one night stand in the back of her limo wasn't strange or outlandish. This was perfectly normal behavior for her, and as her deep brown eyes roamed over his body and face, she decided he wouldn't be the worst person to sleep with. Looking past that initial gawkiness, he could be considered attractive. And his look of shock was pretty enticing too, in that 'adorably clueless' way. Lips pursed, she waited as he mulled over the idea, before answering with a firm denial. He said no? That was the first thing in a matter of weeks to genuinely surprise her. If Katherine was willing to sleep with a man, they never said no. Here Dan stood though, insisting he wanted to get to know her first. He claimed he wanted to understand the real her, why she was the way she was. Oh, so he wanted to understand her? That made the whole situation even worse. Katherine didn't need some unsuccessful writer attempting to analyze her. She didn't need **this**. Shaking her head she didn't even bother giving him a straight answer, hoping he could interpret the slam of the car door as a 'no'.

* * *

Katherine was over Dan Humphrey. He had her interest piqued for a short while, anyone who could deny jumping into the sack with her definitely deserved some respect. After a week of hearing nothing from him however, she was quick to forget all about him. Especially when he claimed he wanted to really become something with her. To find out what she liked, disliked, everything there was to know. Psh. Katherine didn't do that, and she certainly didn't do legitimate relationships. She was relieved it only took three times for him to get the idea, although only having to deny him once would have been a little more ideal. Without his requests of a date, she was free to return to her routine of partying at night and bringing home Damon Salvatore. A man who was pretty much the male version of her. They both only wanted one thing, so their arrangement worked out just fine. _He_ was never concerned about sitting down and talking.

Scowling she dismissed the thought and shoved Dan out of her mind. She had more important things to focus on. Like trying not to fall asleep from boredom as stood with people from her father's company who were all talking about business. With a glass of champagne in her hand, hair in tight tendrils, and a sleek blue gown falling to the ground, there wasn't much Katherine could do to try and keep herself entertained. Unfortunately at this rooftop party she had to be on her best behavior, which was a rare feat for Miss Pierce indeed, who prided herself on being bad. When she absentmindedly spotted Dan Humphrey across the pool, she knew that her day was about to become interesting.

He was an intern, so she didn't question him being there, but she was suspicious as to his motives. He was staring back at her with a smile, eyes never faltering from her. Without excusing herself she traipsed around the glistening blue water and marched right up to him. She instantly accused him of being up to something, but she wasn't met with an answer from him per say. Like a flock of seagulls, a group of kids hurried up to her, speaking in those high, shrill voices. Katherine looked down in horror. She _despised_ kids, and now she was surrounded by a swarm of them. They were all going on about how she should go out with Dan, he was nice, and he'll die of a broken heart if she refused him again. She wasn't exactly paying attention to their words however; she was focused on finding a way to escape this sudden hell. And in her flustered state, with little heads and hands flailing about, the only direction she was able to go with in the direction of the pool.

Losing her balance she grabbed onto Dan, effectively bringing them both splashing into the pool. Well there went her good behavior for the party. Katherine lived up to her bad girl reputation, interrupting the formal get together and bringing all attention to her. Glaring at the group of laughing kids she twisted and furiously splashed some water at Dan, black hair clinging to his forehead. He simply laughed and insisted the children were to blame. Katherine probably would have laughed too had everyone not been staring at them. She felt exposed, probably because she wasn't drunk enough to not feel embarrassment at this point. She simply told Dan to get her out of there, and he complied. Picking her up bridal style he held her close and Katherine clutched back, letting herself be carried out of the pool. After being set down she snapped at a waiter and demanded a towel, before hearing Dan ask her that same agonizing question. He asked her out… yet again. When the towel was finally brought to her, a minute later, she took it and smacked Dan over the head with it. She informed him she hated kids before storming off and out of the public eye.

* * *

Katherine had to snap at Serena at some point. She was to blame for unleashing this plague of Dan Humphrey upon her! Who couldn't seem to just take no for an answer. Serena tried to explain that he appreciated how different Katherine was, how he felt there was more to her than what met the eye, and how he had a history of rehabilitating party girls. Serena thought Dan could be good for her. She dismissed that sentiment with a shrug. Being alone was what was best for Katherine. So after that she quickly suggested they go for a drink, unwilling to keep talking about this guy who had become a prominent part of her life already, simply because he refused to go away.

Halfway down the elevator she realized she had left her phone in the blonde's room, so in annoyance she left Serena on the first floor and went back up. Rushing into the room she was met with who else, Dan Humphrey lurking around. Katherine shouldn't have been surprised anymore by his presence. Anywhere she was, he seemed to be right there after her. This time he stuttered out he was there to clean. Narrowing her eyes she advanced on him, demanding the real reason. He backed away, eyes darting around the room, and he was obviously avoiding something. A something he displayed when he pointed behind her, insisting Eric was streaking down the hallway. Underneath the pointing, she spotted her phone in his hand. Without thinking, she pounced at him, trying to take it from his grasp. Startled and falling against the wall he held it over her head, chuckling and enjoying the way she was jumping all over him.

Clearly attacking him like an animal wasn't working, so she reverted to what she was good at. It hadn't worked back at the limo, but maybe this time around he wouldn't be able to resist. After all she was pressed against him this time. He would be able to feel every crease and curve in her body. Purring out his name she pushed him harder against the wall, looking up into his eyes. For the first time, after every accident and disaster they had together, she was really looking at him. A tinge of softness and excitement in his brown hues, he was really staring back at her. It was oddly unsettling, unusual. Rarely did a guy ever look at her the way Dan was. They barely looked at all. When a girl put out the way she did, they rarely felt the need to pay much attention to anything else. Not that Katherine really cared what guys focused on, but the way Dan was focusing on her. It made her shiver. Noting the limp in his arm she reached up and grabbed her phone, swallowing uncomfortably and thanking him. Another second passed before she turned and got the hell out of there. But not before telling him, one more time, that she would not go out with him.

* * *

It had become second nature now. Nurse a hangover, hang out with friends, deny Dan Humphrey a date. It didn't happen that often, but when it did Katherine was now prepared. Although by now, she would never actually admit it, but she enjoyed seeing what clever way Humphrey could come up with to ask her the same exact question. He was creative and inventive, and it actually made her life just a little bit more interesting. Not that getting drunk, partying, and sleeping with random guys wasn't exhilarating, but Katherine was accustomed to it. Now with requests of a date every now and again interrupting that routine, she found herself excited for the day. Yes, she was actually waking up when the sun was still in the sky now. Her sleeping schedule had mysteriously shifted.

Arriving back home with a few shopping bags in tow, filled with a brand new ensemble of black clothing, she headed straight for her room. With a gasp, she dropped the bags and stared in shock at the scene. Her room was… yellow. Not painted though, from closer inspection Katherine saw they were actually post its. Her room was covered with post its and they all had the same thing written on them. 'Will you go out with me?' Even **this** seemed a little too outlandish for Dan. But she didn't hesitate in grabbing her phone and dialing his number, given to her by Serena. The second he picked up she yelled 'no' and hung up, throwing her phone across the room in annoyance. This would be so much work to get clean. Grumbling in frustration she called out for the maid and stomped to the kitchen for a drink.

* * *

Start of the summer in the Hamptons, and she had to admit, she was a little relieved to get away from it all. Especially since she had a pissed off Blair Waldorf on her tail for 'ruining her life' or whatever. Katherine couldn't even recall what she had done, and at the moment she was too relaxed to care. With a lady working on her nails, the other on her toes, and a margarita in her hand, she was truly happy. As music began though, drifting to her ears from what sounded like it was outside, her state of peace was disrupted. Lifting her head she looked around, long curls flying around her head. The woman kneeling pointed to the window on her left, and Katherine's gaze followed suit.

She hadn't expected it out here in the Hamptons. Why would he be in such an upscale, snooty resort town anyway? As she got up in a huff and threw the window open, there he was however. Dan stood upon a lawn mower, holding speakers in his hands that were blasting the infamous tune Don't You Forget About Me. It was a scene right out of an 80s movie, one she had seen as a little girl and never watched again because of how nauseatingly cheesy it was. Watching him though with that hopeful expression, as tacky as the whole thing was, she found herself wanting to smile. Even scarier than that, she found herself wanting to say yes to him. For the first time in seven tries. He had put so much effort into all his attempts, just for a chance to get to know her. He had done so much for her, more than anyone before him. Katherine dropped her face into her hands as the music continued on, and she tried her best to block it out.

Finding herself with that want… just showed she had to put an end to this. Katherine Pierce was not and would never be a relationship type girl. She loved sleeping around, playing with men as if they were toys, getting wasted to the point she didn't even remember the previous night. He enjoyed reading and writing, discussing old foreign films, and publicly embarrassing her. In what world did Katherine and Dan make a good match? They didn't. So as much fun as it had become for both of them to go back and forth like this, she was sick and tired of it. Now when she lifted her head to stare down at him on the ground, with that look that told him he knew what was coming, it was the first time she felt bad about doing it. That small sober part of her really wanted to give in to him, but she rarely listened to that part. Trying to keep her face expressionless she straightened up and shut the window, Dan's face embedded into her mind. One of complete defeat and heartbreak. Like she had pulled the ground out right from under him. As she collapsed back into her chair and snapped at the woman to get back to it, she appeared unfazed. Honestly, Katherine was upset. Genuinely bummed out about what had just occurred. He seemed so pleased that this would finally be the instant she gave into him, that he had done the most romantic thing he could think of, and it would work. Dan, he was so different from the men she was used to. He was kind, considerate, intelligent, and better than her. She didn't want to deny him again, but they would be both better off. Two people like them weren't meant to be together.

* * *

Katherine's enthusiasm had gone notably downhill after that day. There was just something about turning down such an optimistic guy that had put a damper on her entire week. She had done plenty of evil things in her life that she didn't feel remorse for whatsoever, but denying Dan Humphrey made her feel like the cruelest bitch on the planet. So for a few days she kept to herself, trying to reestablish her way of not caring about things. And when she felt like her old self she finally reemerged for a trip to the beach. She usually hated the sun, true, but not during a summer vacation. After all it's when she got to wear a bikini and flirt with men. For Katherine, it was a beach buffet.

She wouldn't get to the beach though, not today. Because of a stupid obstacle in her way. Dan Humphrey with a blonde on his mouth. They were just standing there on the corner before the entrance to the beach, making out like they weren't even in public, and Katherine found herself simply staring. Wow. She didn't know he had this much passion and energy in him. Now if only that other girl could remove herself from his lips… Narrowing her eyes she cleared her throat and set a hand on her hip, watching expectantly as they pulled apart.

"Caroline?" she snapped, looking at the girl as if she had murdered her puppy. Dan stared at Katherine, giving her a deer in the headlights look, and Caroline was the only one who didn't look like a statue.

"We were just, I mean… it's nothing," she rambled on with a nervous laugh. That high, perky voice made her want to rear her arm back and just whack her across the face.

"Go before I kill you," she said plainly, scrutinizing as the girl nodded. Caroline Forbes smiled at Dan, pecked him on the cheek, and walked off in the direction of the ocean.

She wasn't one to judge if Dan went off and found another girl to get rid of pent up frustration with. Even if it was the resident dumb, annoying blonde. Katherine bounced from guy to guy, so she didn't care, even if it was slightly surprising coming from Dan, who had the reputation of a good, innocent guy. After turning him down so many times he deserved to finally get some action and get his mind off of it. But that didn't mean she wanted him making out with Caroline. She wouldn't have wanted to see him kissing anyone whilst walking down the street. It was awkward, gross, and it pissed her off to be honest. Standing there, eyes locked, she understood that she wanted to be the one kissing him. After all, she was the girl he'd been after for weeks now. Not some cheerleader blonde. God dammit…

"Go out with me!" she shouted in his face, giving him a firm stare. Dan's expression of surprise didn't change, although he did blink to acknowledge he heard her.

Quirking an eyebrow in impatience, she drummed her nails on her hips.

"I—what…"

"Go. Out. With. Me," she repeated, her strong stance not faltering. It didn't even occur how odd this was, for her to actually be demanding a date from him of all people. The words were just slipping out. It was what she wanted, he was now what she wanted, and Katherine always got what she wanted. "This is what you were going for after all? A date. With me," she instructed him with a nod.

Dan finally started showing some reaction in his face, clearing out his dry throat and nodding back.

"Yes, yeah, indeed," he responded, that cocky grin from the first few times he pestered her returning.

"I'm not asking by the way." Rolling her eyes and licking her lips she swept past him, a little proud of herself for actually going through with that. It was uncharacteristic of Katherine Pierce to have a date with Dan Humphrey, but she was so pleased at the thought she didn't care that it was something new and different. And if anyone said something about it she would be forced to torture him or her.

Running up behind her Dan leaned over her shoulder and whispered in her ear, "So you'll go out with me?" She didn't even need to turn and look to be able to know that he was still wearing that smirk.

Katherine remained silent until they reached the hot sand, ocean breeze finding them and sweeping all around. As her eyes roamed across the expanse of people with umbrellas and blankets she figured, Dan deserved that answer. He'd vied for it eight times now, and really, was she _that_ cruel to deny him once more? Sighing and turning back to him, she returned his smirk.

"Yes." Scoffing at finally giving in to him, she pushed his shoulder with more force than she realized, sending him stumbling backwards into the sand. Dan's laughter echoed behind her as she moved forward and slid her sunglasses down, ready to chill on the beach as if none of this had happened. Just because she was now going on a date with him didn't mean she needed to stick back, help him up, and start being a nice person. After karaoke, a mail cart, the back of a limo, a pool and _freaking_ kids, stealing phones, post-its, and a sickening rendition of Don't You Forget About Me, Katherine was finally going out with Dan. And a small part of her, sober or not, assured her it would all be worth it.

* * *

**a/n:** based off an rp thread with different characters, this is very much au in that they're both human, both living in new york, etc. review and tell me what you thought, this is the first i've written in a while.


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